> So much to learn and consider
Great point, and you've put your finger on one of the durable 'constants' of boating, in my opinion (no matter your experience level).
LI North Shore is an interesting option, but I'd be sure to check the ferry schedules to see if that will work with your cruising plans / work schedule / etc.
Not sure about your question on the slip ownership taxes, but I'd be willing to guess they are 'on the table' up in Hartford (based on recent events here in CT with raising taxes etc) if not already in place (since it sounds like real property). Luckily the boat property tax didn't make it in (this time around, anyway).